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Named reactions

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Search synthesis

Saxitoxin

"Dedicated to Professor R. B. Woodward on the occasion of his 60th birthday."

Chemical structure of Saxitoxin
C10H17N7O4
Author Yoshito Kishi
Publication year 1977
Synthesis type Total synthesis
Number of steps 19 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
HO(CH2)3OH, TsOH
PhMe
Reflux
Chemical structure
NH2NH2
MeOH, H2O
Reflux, 74% (2 steps)
Chemical structure
P2S5
PhH
Chemical structure + Chemical structure
NaHCO3
CH2Cl2
Reflux

See the Eschenmoser Sulfide Contraction
Chemical structure
KOH
MeOH
50 °C, 50% (3 steps)
Chemical structure + Chemical structure
Si(NCS)4
PhH
RT, 75%
Chemical structure
NH2NH2
MeOH, H2O
RT
Chemical structure
NOCl
MeOH
-50 °C
Chemical structure
PhH
90 °C

See the Curtius Rearrangement
Chemical structure
NH3
PhH
RT, 75% (4 steps)
Chemical structure
HS(CH2)3SH, BF3.OEt2
MeCN
RT, 63%
Chemical structure
(CF3CO)2O
AcOH
50 °C, 18 h, 50%
Chemical structure
Et3O+ BF4-, NaHCO3
CH2Cl2
RT
Chemical structure
EtCO2NH4
135 °C, 33% (2 steps)
Chemical structure
BCl3
CH2Cl2
0 °C
Chemical structure
Ac2O
Pyr
RT, 75% (2 steps)
Chemical structure
NBS
MeCN, H2O
15 °C
Chemical structure
MeOH
100 °C, 30% (2 steps)
Chemical structure
ClSO2NCO
HCO2H
5 °C, 50%
Chemical structure

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